Jay Cline wrote:When you used your wife's computer (and it worked) were you using her email address or the same one that has the problem? After discussing this with our son he suggested that your email address might have been flagged as spam by an SMTP server. You can test it by signing up for a Gmail account.

I went into my account and used the same email account that has all the problems on my MacBook.

Same problems with my Gmail account and my Outlook account.

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Always burn your bridges. You never know who's coming up from behind.

Jay Cline wrote:Would it be too much to ask for you to give us a brief on everything you've tried thus far? What works and doesn't work.

Jay, that's a perfectly reasonable request but I'm tired of it all. Give me some time and I'll see what I can do. But the real problem with creating a list of attempted fixes is that sometimes a fix works and then it doesn't. More than once I got things working and then that fix stopped working.

I'm burned out.

UPDATE! For the last 24 hours I've been able to send emails with multiple recipients, emails with links, and emails with attachments from Mail using my Outlook account. Of course, my Outlook account had failed earlier but it seems to be working for now. If it stops working I'll get back to you.

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Always burn your bridges. You never know who's coming up from behind.